Operation Wolf
by T-rahz
Summary: Henry suspects that Regina has feelings for Ruby and devises a plan and enlists the help of Emma to get the two together so that his mom can finally be happy. Worry not, it's SwanQueen all the way.
1. Chapter 1

**A/n: So this is my first time writing OUAT Fanfiction. My gf got me started on the show a couple weeks ago because she's been borderline obsessed with it since its inception (s** **orry darling) and now I'm possibly just as involved as she is. I'm quite nervous about offering this to the SwanQueen fandom cuz it's possibly the strongest and most talented fandom ever! So please bear with my novice attempt at writing. Thank you to my love, my darling, my beta Iwantafarnsworth, this one's for you my sweet. Do enjoy :)**

* * *

The first time it happened they were having breakfast. He was having a stack of Granny's infamous pancakes together with a hot cocoa, with cinnamon of course. Hook and Emma were at the counter having coffee while he and his mom were sitting at the booth by the window. Hook kept leaning closer and closer to Emma as their conversation progressed, clearly flirting with his incorrigible pirate charm. But that's not what caught Henry's attention. Ruby was on the other side of the counter, opposite Emma and Hook, dressed in another of her stylishly short red skirts that showed off her endless legs. Her smile was radiant as ever this morning, one of his favourite things about her. It was hard to miss the look in his mother's eyes as she looked fondly in Ruby's direction. A mixture of interest, affection and what might be possibly jealousy swimming in those deep brown orbs. He smiled at his mom, knowing that she was oblivious to the fact that he was observing her. After all that his mom had been through, she deserved some happiness, someone to make her smile, someone to love her, someone to be hers. Emma already had Hook and his dad. But his mom had never shown any kind of interest in anyone. That is, until now. If his mom liked Ruby, then he was going to make every effort to make that happen. He didn't care that Ruby was not a guy. She was kind, sweet, funny and had the biggest heart ever. Plus, she was also a werewolf. What could possibly be cooler than THAT? Operation Wolf, that's what he would call it.

* * *

Henry sat in his room later that day trying to devise a plan to get his mom and Ruby together. Their interactions had never been much; only brief moments at the diner when she would take their order or his mom would complain about the overpriced lasagna. Aside from that, there was nothing he could really work with. He drew up a table on a blank piece of paper and tried to write down things his mom liked to do in one column and things he knew about Ruby's hobbies in the other column. After about an hour of intense thinking, chewing on the end of his pencil and staring at that spot on the far wall, he looked down at his table, disappointed by it's scanty fill. There were only a few things on Ruby's side as he really didn't know much about what the wolf did outside of the diner. His mom's list was even shorter as there were precious few things in this world that she actually enjoyed. He let out a frustrated sigh. This was going to be harder than he thought.

* * *

The next time he noticed it was two days later. He was walking down by the docks with Emma and Ruby, trying to gather information about the girl. He was glad when Ruby had said her shift was over and that she was going for a walk. He had been at the diner with Emma and jumped at the opportunity to get to know the pretty waitress better. He listened carefully to their conversation, enjoying the way Ruby's voice sounded. As if luck were on his side, he spotted his other mom walking on the other side of the dock and pulled Emma and Ruby along to go meet her. That's when he saw the look in his mom's eyes again. That affectionate longing mixed with a bit of turmoil. He couldn't imagine the war waging in his mother's heart. After all, Ruby was Red, Snow White's best friend. And Snow White was the Evil Queen's sworn enemy. She was probably worried that Ruby would not like her back because of their past enmity. But here now, they were just Ruby and Regina. It would be up to him to find a way to make Ruby see her as more than just the Evil Queen. To change that look in his mom's eyes from one of pain and loneliness to one of love and acceptance.

* * *

All through dinner that night he couldn't stop thinking about ways to make his mom look good. Situations where she could get a chance to be the hero. Sure there had been many instances over the last couple of years when his mom's trustworthiness had been more than questionable but there had also been those times when she had been the one to save the day, to save them all. Surely Ruby couldn't have forgotten that so soon. Either way, he couldn't exactly create another life and death situation for his mom to rescue the town. There had to be another way.

"Henry? Is everything alright?" His mom's voice broke through his thoughts.

"I'm sorry, what mom?"

"I was asking how was your day today, but you seemed lost to the world for a moment there. Is everything ok?" She asked, kindness and concern reflected in her brown eyes. He loved the way his mom looked at him. She could be at the brink of bringing down the world but the moment her attention turned to him everything else would be wiped aside and all he would see was the love she had for him.

"I had a nice time with mom. We had a late lunch at Granny's and then went for that walk on the docks with Ruby," he replied, pausing for a moment, "Ruby is really nice, I like spending time with her," he added in, trying to let his mom know that he was ok with her having feelings for Ruby.

His mom's forehead crinkled a little as she regarded him with what looked like a bit of surprise, possibly wondering why he had said that. He didn't mind that she might suspect that he knew about her interest in the waitress, what mattered was that now she knew that he would be ok with it.

* * *

The next day Henry was sitting on the swing at the park staring out at the playground but not really seeing anything as his mind was again racing trying to find solutions to the dilemma at hand. He could maybe take his mom's phone and send Ruby a text inviting her on a date. He pondered on that briefly before shaking his head, dismissing it. That would be too forward. Plus, if Ruby refused then his mom would be humiliated. His brow furrowed into a thin line again as he thought hard at the dirt on the ground. Maybe he could ask Robin to take his mom on a date at Granny's while Ruby is there. If the waitress saw his mom showing interest in someone else maybe that would make her feel jealous and realize that she had feelings for his mom. Again he dismissed the idea from his head. He knew Robin actually liked his mom. He didn't want the poor man to be led on by his antics. He huffed out a dejected sigh, not noticing Emma quietly seating herself in the swing next to his.

"That clump of dirt bothering you there, kid?"

"Huh? what?" he looked up, startled.

"I dunno, you were staring at the ground so intently like that clump of dirt just stole your dog or something. You alright kiddo?" Emma asked, not unlike his mom's concerned question the night before. He thought for a moment whether he should tell Emma what was on his mind or not. She was his mom after all, maybe he could tell her some of it and see how she responds.

"Sooo…" he began, "I have this friend…." he paused.

"A friend, huh?" she encouraged him on.

"Yeah, this, uh, friend, likes another of my friends. Like, _like_ , like." he continued cautiously, pausing again to glance at her. She nodded, urging him on.

"My friend doesn't know if the other friend sees him that way but I know they'd be good together, I just need to know what the other friend thinks, so I can help my friend win her over," he finished, quite proud that he had avoided telling her all the details but still got the gist of the problem across.

His mom opened and closed her mouth, her expression like a deer caught in headlights. She blinked and looked away briefly before settling her eyes on him again. She cleared her throat before beginning to talk again.

"Um, did Regina by chance give you the talk as yet?" she asked tentatively. He was confused. What talk was she referring to? How did she know he was talking about his mom? He ran through what he had said to her in his mind, checking to see if he had unintentionally hinted to her that it was Regina he had been referring to. Nope, his explanation was airtight. There was no way she could have known. He looked up at her questioningly, "what _talk_?" He asked, emphasizing the word talk.

"You know, _the_ talk. About liking girls and stuff like that," she responded, clearly out of her element here. His brow creased further as he regarded her before his eyes widened in realization. She thought he liked a girl! She thought his problem was related to himself!

"Mom no, this is not about me, it's about my friend. Honest!"

"Right, a _friend_. It's okay Henry, you're growing up. It's normal to start liking girls."

"No mom I promise, it's really not about me."

"Come on kiddo, it's nothing to be embarrassed about." she moved to pull his swing close to hers to give him a hug but he jumped off it to face her. "I think my mom has a crush on Ruby and I want to find a way to get them together!" He rattled out clasping his hands over his mouth as the last bit escaped his lips, not believing that he had just blurted everything out like that. He looked up at his mom, seeing a mixture of something he couldn't quite understand swirl through her eyes briefly before being quickly replaced with one of interest and a quirk of her eyebrow.

"Your mom and Red, huh?" she asked, something different in her voice. Henry was worried. What did that look and the sound in her voice mean? Was she homophobic? Did the thought of his mom liking another woman repel his biological mother? Emma's voice brought him out of his troubled thoughts.

"I think it's cool that your mom likes Ruby. It's about time she showed interest in _someone_ in this place. How do you plan on getting them together?" she asked.

Henry looked up at her and smiled, his previous worries washed away by her words.

"I dunno. I've been trying to think of ways but nothing seems like the right plan. At first I thought of texting Ruby with my mom's phone but that's too risky and would embarrass my mom into going into hiding again. Then I was thinking of having Robin take her out on a date at Granny's just to make Ruby jealous, but Robin actually likes my mom so that wouldn't work very well. I need to get someone who has no feelings like that for my mom to take her out so that Ruby can realize her feelings for her." he explained.

"I guess that could work, but how do you know that Ruby has feelings for her? And besides, who do you know that doesn't have feelings for your mom and who she would agree on going on a date with?" Emma asked, looking across at him as he sat back on his swing. He pondered on it for a bit, mentally running through all the possible eligible bachelors in Storybrooke in his mind. He remained silently thinking for a bit before an idea so brilliant struck him, he almost fell backwards off the swing as he rushed to stand up again and face Emma.

"I got it!" he exclaimed, grinning at her.

"Okay, what is it?" she asked, eyeing him suspiciously. He silently looked at her, not sure how to say it, a silly grin still plastered on his face and a mischievous glint in his eyes. He could see Emma trying to figure out what he was thinking when her eyes widened. She had figured it out.

"No. no way, kid. Not happening." she refused.

"Come onnnnnn, you're perfect. I can trust you AND you don't have feelings for my mom. Plus, you're a woman, so she might be more inclined to say yes. Come on, please? For me? I want to see my mom happy again." he pleaded, putting on his saddest begging face. He looked at her as she thought it over, not missing the glimmer of that strange look again crossing her face before she reluctantly agreed.

"Fine, only for you. What do I have to do?"

"Yes!" he exclaimed victoriously. "For now, not much, maybe have lunch with my mom when Ruby is there and flirt with her a little?" he suggested.

 **A/n Hope you enjoyed! Please share your thoughts, suggestions and comments! Thanks for reading!**


	2. Flirting with the Queen

**A/n: thank you so much for all your comments, follows and likes :) I received a few worried pm's that I had the story listed as SwanQueen but it was actually RedQueen I assure you, this one is definitely SQ :) and on that note, happy Swan Queen week!**

 **Thank you and happy birth week to my girlfriend/beta Iwantafarnsworth :) I love you**

"Flirting with Regina, this is gonna be interesting," Emma commented.

"We can have lunch together and you can do flirty stuff when Ruby is around. That way she'll notice and get jealous and maybe ask my mom out," he suggested, excited to put his plan into action.

"Ok kid, we'll see how it goes," she agreed, still sounding reluctant about what she had just gotten herself into. Henry could hear a tinge of worry in his mom's voice but just chalked it up to her being nervous about having to fake flirt with Regina.

"Sooooo, when are you going to ask her out?" He pressed on.

"What? I thought you said I just had to flirt with her a little! When did I level up to asking her out?" Emma asked wide-eyed.

"To lunch I mean. You have to call and ask her to join us for lunch. It's not like a date, just lunch. With us," he reassured her, "today," he added in, looking eagerly at her.

She huffed out audibly, reaching into her jacket to retrieve her phone. Henry looked on as Emma quickly dialed his mother and waited for it to connect. He could faintly hear her voice coming through the tiny phone speaker.

"Miss Swan? To what do I owe the pleasure?" He heard her say.

"Um, Henry and I were wondering if you'd like to join us for lunch today. At Granny's," Emma asked, her voice sounding small. He nodded his head at her in encouragement.

There was silence on the other end, before his mother replied, "I'm not one to take last minute invitations, Ms Swan, but you're lucky that the only person I'd do it for is Henry. See you at Granny's in an hour." Before Emma could respond, the line clicked dead.

An hour later found Henry and Emma seated at a booth in Granny's diner, the waitress in question flitting around in her mini red skirt and tight white shirt. Henry quietly observed the woman, her long dark hair with bright red highlights flowing gracefully down her shoulders, her smile radiant as ever as she chatted with customers around the diner. He really liked Ruby, she was definitely one of his favourite persons in Storybrooke, aside from his two moms of course. He shifted his attention back to Emma, who he noticed was also following the young waitress with her eyes. Her forehead was creased slightly and her eyes had that strange look again. Before he could think more into it, the door chimed, signaling the entry of his mother. Both he and Emma stood to welcome her as she made her way to the table. He leaned in to give her a light hug while Emma waited for the queen to take her seat before returning to hers.

"It's nice of you to join us on such short notice, Regina," Emma greeted.

"Well, I had to eat, and what better way to do so than in the company of my son?" she responded. Emma nodded but made no effort to carry the conversation further. Henry looked between them, shaking his head in slight frustration. He kicked Emma under the table and glared at her to do something. Emma glared back and ground her teeth.

"What do you feel like eating?" She asked, locking eyes with Regina before guiding her gaze to the suggestively clad Ruby. Regina quirked an eyebrow, her eyes never leaving Emma's to follow the direction in which the younger woman was suggesting. Henry rolled his eyes and mentally facepalmed himself. Emma was not supposed to let Regina know that she knew about Ruby. Thankfully his mom had not caught on to what Emma was hinting at.

The waitress came over to take their order, shooting Henry her signature bright smile. He couldn't help but smile back at her. He kicked Emma again under the table, a not-so-gentle reminder to flirt with his mom. She took the hint and leaned across to Regina, lightly resting her hand on the woman's forearm.

"Have you decided yet?" She asked softly. His mother looked shocked by Emma's touch and faltered a little in her attempt to make yet another snide remark at the price of the lasagna. She abandoned the attempt and resigned herself to ordering said dish. Henry observed the amused look on Ruby's face at the interaction, disappointed that there was no jealousy in her eyes. Maybe she needed a little more pushing. Even after his mother ordered, Emma's hand remained resting on her arm, both women quietly regarding each other. Emma didn't seem keen on ordering so he took charge and ordered them both burgers and fries, much to his mother's disgust.

The waitress returned a few minutes later with their drinks, an intrigued look on her face as she realized that Emma's hand was still resting on Regina's. Her arrival shook both women out of the moment and Emma sheepishly retreated her hand, grabbing hold of her soda and sucking on the straw intently. Henry was a bit confused at both his mothers' behaviors but figured it was because they were not used to any kind of friendly interaction. When their food arrived a short while later, the three of them tucked in quietly, all seemingly lost in their own thoughts. Henry looked between his moms, ever so often each looking up at the other but never at the same time. Again he chalked up the awkwardness to their unfamiliarity with their current situation and left them to it. Soon enough they'd get used to it and their flirtations would become more believable.

When Ruby returned later with the bill he didn't have to kick Emma under the table to act as she quickly reached forward for the check.

"Ms. Swan, as flattered as I am, I pay your wages, surely I can buy lunch." Regina offered, swatting Emma's hand away and reaching into her bag for her wallet. Emma's hand was on her forearm again, her thumb brushing gently against the soft skin there.

"With all due respect madam mayor, this one's on me," she dismissed the older woman's offer, quickly handing Ruby her credit card. The smirk on Ruby's face didn't go unnoticed by Henry as she swiped the card and punched in the amount. He smiled inwardly, she was finally taking notice.


End file.
